South B Street

From the San Mateo Area Chamber of Commerce (https://sanmateochamber.org/sept-fest/): 2026 September Arts & Culture Fest Mark your calendar for Saturday, September 26th, 2026, 11am - 6pm! Join us in the […]

From the City of San Mateo: Learn more about Soccer Celebrations and participating businesses HERE All 2026 San Mateo Soccer-related events: Event Date Time Location Soccer Social Pop-Up Friday, June […]

From the City of San Mateo: Learn more about Soccer Celebrations and participating businesses HERE All 2026 San Mateo Soccer-related events: Event Date Time Location Soccer Social Pop-Up Friday, June […]

Kick off your SUPER weekend at our San Mateo Sports Warm Up on Saturday, February 7th from 1–3 pm! We’re bringing the big-game energy to the heart of Downtown with a free, family-friendly afternoon of play featuring a very special appearance by the back-to-back State Champion CSM Bulldogs! Come meet and greet some players from […]

Celebrate Lunar New Year on Saturday, January 24th in Downtown San Mateo! Stay tuned for more information! Brought to you by the DSMA and Florian Orthodontics. This family-friendly event on B Street (between 1st and 2nd Ave) will showcase a Lion Dance performance from Lion Dance Me at noon, plus community booths with activities, red […]

Sorry! The final HEAD WEST San Mateo event for 2025 has been canceled due to the weather. Keep an eye out for 2026 dates! About HEAD WEST: HEAD WEST provides a marketplace for emerging + established local brands and small businesses to have physical selling space multiple times per month at various neighborhood venues. From […]

SPECIAL DATE! Shop Small in Downtown San Mateo with HEAD WEST Marketplace. Visit Downtown San Mateo's B Street for HEAD WEST Marketplace on the third Sunday of every month in […]

From the San Mateo Area Chamber of Commerce (https://sanmateochamber.org/sept-fest/): September Arts & Culture Fest The Best Street Festival on the Peninsula is Back! Presented by the San Mateo Area Chamber […]